EP0825987A1 - 1-fluorisoquinoline derivatives and the use thereof in liquid crystalline mixtures - Google Patents
1-fluorisoquinoline derivatives and the use thereof in liquid crystalline mixturesInfo
- Publication number
- EP0825987A1 EP0825987A1 EP96916035A EP96916035A EP0825987A1 EP 0825987 A1 EP0825987 A1 EP 0825987A1 EP 96916035 A EP96916035 A EP 96916035A EP 96916035 A EP96916035 A EP 96916035A EP 0825987 A1 EP0825987 A1 EP 0825987A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ich
- phe
- pyr
- pym
- naf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- YYMRKWBKEKCKHM-UHFFFAOYSA-N 1-fluoroisoquinoline Chemical class C1=CC=C2C(F)=NC=CC2=C1 YYMRKWBKEKCKHM-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 title claims description 37
- 239000007788 liquid Substances 0.000 title abstract description 3
- -1 1,4-phenylene, pyrimidine-2,5-diyl Chemical group 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 5
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- GKZIWHRNKRBEOH-HOTGVXAUSA-N Phe-Phe Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)C1=CC=CC=C1 GKZIWHRNKRBEOH-HOTGVXAUSA-N 0.000 claims description 3
- 108010073025 phenylalanylphenylalanine Proteins 0.000 claims description 3
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000000185 1,3-diols Chemical class 0.000 description 2
- ZYMKXYLNNRFQKN-UHFFFAOYSA-N 1-fluoro-3-(4-octoxyphenyl)-7-octylisoquinoline Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC2=CC=C(CCCCCCCC)C=C2C(F)=N1 ZYMKXYLNNRFQKN-UHFFFAOYSA-N 0.000 description 2
- DUQIEZVLADZHAX-UHFFFAOYSA-N 1-fluoro-3-octoxy-7-(5-octoxypyridin-2-yl)isoquinoline Chemical compound N1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C=C(OCCCCCCCC)N=C2F)C2=C1 DUQIEZVLADZHAX-UHFFFAOYSA-N 0.000 description 2
- OSNNDDGQNXDFNC-UHFFFAOYSA-N 1-fluoro-3-octoxy-7-(5-octoxypyrimidin-2-yl)isoquinoline Chemical compound N1=CC(OCCCCCCCC)=CN=C1C1=CC=C(C=C(OCCCCCCCC)N=C2F)C2=C1 OSNNDDGQNXDFNC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 150000001564 phenyl benzoates Chemical class 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SFOYQZYQTQDRIY-UHFFFAOYSA-N 1-chloro-3-iodopropane Chemical compound ClCCCI SFOYQZYQTQDRIY-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- GWRVDXMHYYHWCZ-UHFFFAOYSA-N 2-(1-fluoro-3-octoxyisoquinolin-7-yl)pyrimidin-5-ol Chemical compound C1=C2C(F)=NC(OCCCCCCCC)=CC2=CC=C1C1=NC=C(O)C=N1 GWRVDXMHYYHWCZ-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- BKBMLKUHAVKFRY-UHFFFAOYSA-N 4-(1-fluoro-7-octylisoquinolin-3-yl)phenol Chemical compound CCCCCCCCc1ccc2cc(nc(F)c2c1)-c1ccc(O)cc1 BKBMLKUHAVKFRY-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CUJXMPSIMXAEKQ-UHFFFAOYSA-N 6-(1-fluoro-3-octoxyisoquinolin-7-yl)pyridin-3-ol Chemical compound C1=C2C(F)=NC(OCCCCCCCC)=CC2=CC=C1C1=CC=C(O)C=N1 CUJXMPSIMXAEKQ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-DRSKVUCWSA-N C1=C(C=CC2=CC(=CC=C12)[2H])[2H] Chemical compound C1=C(C=CC2=CC(=CC=C12)[2H])[2H] UFWIBTONFRDIAS-DRSKVUCWSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical class OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
Definitions
- optically active, inclined smectic (ferroelectric) liquid crystals have also recently been used in commercial display devices.
- connection that form inclined or orthogonal smectic phases and are themselves optically active, or one can by doping compounds that form such smectic phases, but not optically active are, induce ferroelectric smectic phases with optically active compounds.
- the desired phase should be stable over the largest possible temperature range.
- a uniform planar orientation of the liquid crystals is necessary to achieve a good contrast ratio in electro-optical components.
- a good orientation in the S A and S * c phase can be found e.g. B. achieve if the phase sequence of the liquid crystal mixture with decreasing temperature is: Isotropic ⁇ N * ⁇ S A ⁇ S * c
- the pitch (pitch of the helix) in the N * phase is very large (greater than 10 ⁇ m) or, even better, completely compensated (see, for example, BT Matsumoto et al., P. 468-470, Proc. of the 6th Int. Display Research Conf., Japan Display, Sept. 30 - Oct. 2, 1986, Tokyo, Japan; M. Murakami et al., ibid. pp. 344 - p. 347).
- This is achieved e.g. B. by adding to the chiral liquid crystal mixture which in the N * phase z. B. has a left-handed helix, one or more optically active dopants that induce a right-handed helix in such amounts that the helix is compensated.
- the optical switching time T [ps] of ferroelectric liquid crystal systems which should be as short as possible, depends on the rotational viscosity of the system y [mPas], the spontaneous polarization P s [nC / cm 2 ] and the electric field strength E [V / m] the relationship
- the ferroelectric Display medium Since the field strength E is determined by the distance between the electrodes in the electro-optical component and by the applied voltage, the ferroelectric Display medium must be low-viscosity and have a high spontaneous polarization so that a short switching time is achieved.
- a small optical anisotropy ⁇ preferably “0, 13, and a low positive or preferably negative dielectric anisotropy ⁇ E is required (see, for example, ST Lagerwall et al.,“ Ferroelectric Liquid Crystals for Displays ”SID Symposium , Oct. Meeting 1985, San Diego, Ca, USA). All of these requirements can only be met with mixtures of several components.
- the basis (or matrix) used is preferably compounds which, if possible, themselves already have the desired phase sequence 1 ⁇ N ⁇ S A ⁇ S c .
- the DHF effect was described by Bl Ostrovski in Advances in Liquid Crystal Research and Applications, Oxford / Budapest 1980, 469 ff.,
- the PSFLCD effect is described in DE-A 39 20 625 and EP-A 0 405 346.
- a liquid crystal material with a short S c pitch is required to use these effects.
- the object of the present invention was therefore to provide new compounds which are suitable in liquid-crystalline mixtures for improving the property profile of these mixtures.
- the invention therefore relates to compounds of the formula (I)
- R 1 , R 2 are identical or different hydrogen, -CN, -F, -Cl, -CF 3 ,
- a 1 , A 2 , A 3 , A 4 are identical or different 1, 4-phenylene, where one or more H atoms can be replaced by F, Cl and / or CN, pyrazine-2,5-diyl, one or two H atoms can be replaced by F, Cl and / or CN, pyridazine-3,6-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, pyridine-2,5- diyl, where one or more H atoms can be replaced by F, Cl and / or CN, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, trans- 1, 4-cyclohexylene, where one or two H atoms can be replaced by CN and / or CH 3 , (1, 3,4) -Thiadiazol-2,5-diyl, 1, 3-dioxane-2,5- diyl, 1,
- a, b, c, d, e, f are zero or one, with the proviso that the sum of b, c, d and e must be 0, 1 or 2.
- the compounds of the formula (I) are colorless in the pure state and generally form liquid-crystalline mesophases in a temperature range which is favorable for electro-optical use. They are stable chemically, thermally and against light.
- the compounds of formula (I) are particularly suitable for influencing the dielectric anisotropy ⁇ e of liquid-crystalline mixtures in the direction of higher negative values even in small amounts.
- Preferred compounds of the general formula (I) are those in which the symbols and indices have the following meanings:
- R 1 , R 2 are identical or different hydrogen, -CN, -F, -Cl, -CF 3 ,
- -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F or a straight-chain or branched alkyl radical having 1 to 18 carbon atoms (with or without an asymmetric carbon atom), one or more CH 2 - groups by -O-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH CH-, -C ⁇ C-, cyclopropane-1, 2- diyl, -Si (CH 3 ) 2 - or trans-1, 4-cyclohexylene can be replaced, with the proviso that oxygen atoms must not be bonded directly to one another, and / or where one or more H atoms of the alkyl radical are replaced by -F , -Cl, -OR 3 , -OCN or -N 3 may be substituted, or one of the following groups (optically active or racemic):
- M 1 , M 2 , M 3 , M 4 , M 5 , M 6 are identical or different -O-, -CO-, -CO-O-,
- a 1 , A 2 , A 3 , A 4 are identical or different 1, 4-phenylene, where one or more H atoms can be replaced by F, Cl and / or CN, pyrazine-2,5-diyl, one or two H atoms can be replaced by F, Cl and / or CN, pyridazine-3,6-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, pyridine-2,5- diyl, where one or more H atoms can be replaced by F, Cl and / or CN, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, trans- 1, 4-cyclohexylene, where one or two H atoms can be replaced by CN and / or CH 3 , (1, 3,4) -Thiadiazol-2,5-diyl, 1, 3-dioxane-2,5- diyl,
- a, b, c, d, e, f are zero or one, with the proviso that the sum of b, c, d and e is 0, 1 or 2.
- R 1 , R 2 are identical or different hydrogen, -CN, -F, -Cl, -CF 3 ,
- -CHF 2 , -CH 2 F, -OCF 3 , -OCHF 2 , -OCH 2 F or a straight-chain or branched alkyl radical with 1 to 16 carbon atoms (with or without asymmetric carbon atom), also one, two or three CH 2 groups by -O-, -CO-, -O-CO-, -CO-O-, -CH CH-, cyclopropane-1, 2-diyl, -Si (CH 3 ) 2 - or trans -1, 4-Cyclohexylene can be replaced, with the proviso that oxygen atoms must not be bonded directly to one another, and / or wherein one or more H atoms of the alkyl radical can be substituted by -F, -Cl or -OR 3 , or also one of the following groups (optically active or racemic):
- M 1 , M 2 , M 3 , M 4 , M 5 , M 6 are identical or different -O-, -CO-, -CO-O-,
- a 1 , A 2 , A 3 , A 4 are identical or different 1, 4-phenylene, where one, two or three H atoms can be replaced by F, Cl and / or CN, pyridine-2,5-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, Cl and / or CN, trans-1, 4-cyclohexylene, where one or two H atoms can be replaced by CN and / or CH 3 , (1, 3,4) -thiadiazole-2,5-diyl or naphthalene-2,6-diyl, one or two H atoms can be replaced by F, Cl and / or CN;
- a, b, c, d, e, f are zero or one, with the proviso that the sum of b, c, d and e is 0, 1 or 2.
- R 3 , R 4 are the same or different hydrogen or a straight chain
- Alkyl radical with 1-9 C atoms it also being possible for one or more CH 2 groups to be replaced by —O—, with the proviso that oxygen atoms must not be bonded directly to one another;
- M 1 , M 2 , M 3 , M 4 , M 5 , M 6 are identical or different -O-, -CO-, -CO-O-,
- a 1 , A 2 , A 3 , A 4 are identical or different 1, 4-phenylene, where one, two or three H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H- Atoms are replaced by F. can, pyrimidine-2,5-diyl, trans-1, 4-cyclohexylene, where one or two H atoms can be replaced by CN and / or CH 3 or naphthalene-2,6-d.yl, where one or two H atoms can be replaced by F;
- a, b, c, d, e, f are zero or one, with the proviso that the sum of b, c, d and e is 0, 1 or 2.
- TDZ (1, 3,4) -Thiadiazol-2,5-diyl mean and M 1 , M 6 , R 1 , R 2 have the meanings given in formula (I).
- the compounds according to the invention are prepared by methods known per se from the literature, as used in standard works for organic synthesis, e.g. B. Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart.
- the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made here of variants which are known per se and are not mentioned here in detail. If desired, the starting materials can also be formed in situ, in such a way that they are not isolated from the reaction mixture, but instead are immediately reacted further to give the compounds of the formula (I).
- the group P 9 is the group R 1 (-M 1 ) a (-A 1 -M 2 ) b (-A 2 -M 3 ) c or a suitable, optionally protected precursor thereof, which is known per se in later steps , methods familiar to the person skilled in the art can be transferred into this grouping.
- P 9 can be a perfluoroalkyl sulfonate, the group R 1 (-M 1 ) a (-A 1 -M 2 ) b (-A 2 -M 3 ) c then being introduced by coupling with, for example, a corresponding boronic acid.
- R x is the grouping (-M 4 -A 3 ) d (-M 5 -A 4 ) e (-M 6 ) f -R 2 or a suitable, possibly protected precursor thereof, which in later steps according to known, methods familiar to the person skilled in the art can be converted into this grouping.
- DE-A 26 41 724 for compounds with pyrimidine-2,5-diyl groups;
- DE-A 40 26 223 and EP-A 03 91 203 for compounds with pyridine-2,5-diyl groups;
- DE-A 32 31 462 for compounds with pyridazine-3,6-diyl groups; EP-A 309 514 for compounds with (1, 3,4) thiadiazole-2-5-diyl groups;
- WO-A 92/16500 for naphthalene-2,6-diyl groups;
- DE-A 37 10 890 for bicyclo [2.2.2.] Octane-1,4-diyl groups;
- K. Seto et al Journal of the Chemical Society, Chemical Communications 1988, 56 for di
- disubstituted pyridines disubstituted pyrazines, disubstituted pyrimidines and disubstituted pyridazines
- disubstituted pyridines disubstituted pyrazines
- disubstituted pyrimidines disubstituted pyridazines
- Dioxane derivatives are expediently prepared by reacting an appropriate aldehyde (or one of its reactive derivatives) with a corresponding 1,3-diol (or one of its reactive derivatives), preferably in the presence of an inert solvent, such as benzene or toluene, and / or a catalyst, e.g. a strong acid, such as sulfuric acid, benzene or p-toluenesulfonic acid, at temperatures between about 20 ° C and about 150 ° C, preferably between 80 ° C and 120 ° C.
- Acetals are primarily suitable as reactive derivatives of the starting materials.
- aldehydes and 1,3-diols mentioned and their reactive derivatives are known, and in some cases they can be prepared without difficulty using standard methods of organic chemistry from the literature Connections are made.
- the aldehydes can be obtained by oxidation of corresponding alcohols or by reduction of nitrites or corresponding carboxylic acids or their derivatives, and the diols can be obtained by reducing corresponding diesters.
- Compounds in which an aromatic ring is substituted by at least one F atom can also be obtained from the corresponding diazonium salts by exchanging the diazonium group for a fluorine atom, e.g. according to the methods of Balz and Schiemann.
- the acid halides are also particularly suitable as reactive derivatives of the carboxylic acids mentioned the anhydrides, for example also mixed anhydrides, azides or esters, in particular alkyl esters with 1 -4 C atoms in the alkyl group.
- Suitable reactive derivatives of the alcohols or phenols mentioned are in particular the corresponding metal alcoholates or phenolates, preferably an alkali metal, such as sodium or potassium.
- esterification is advantageously carried out in the presence of an inert solvent.
- Ethers such as diethyl ether, di-n-butyl ether, THF (tetrahydrofuran), dioxane or anisole, ketones such as acetone, butanone or cyclohexanone, amides such as DMF or are particularly suitable
- Phosphoric acid hexamethyl triamide Phosphoric acid hexamethyl triamide
- hydrocarbons such as benzene, toluene or xylene
- halogenated hydrocarbons such as carbon tetrachloride, dichloromethane or tetrachlorethylene
- sulfoxides such as dimethyl sulfoxide or sulfolane.
- Ethers of the formula (I) can be obtained by etherification of corresponding hydroxyl compounds, preferably corresponding phenols, the hydroxyl compound advantageously first being converted into a corresponding metal derivative, for example by treatment with NaH, NaNH 2 , NaOH, KOH, Na 2 CO 3 or K 2 CO 3 is converted into the corresponding alkali metal alcoholate or alkali metal phenolate.
- alkyl halide alkyl sulfonate or dialkyl sulfate
- an inert solvent such as acetone, 1, 2-dimethoxyethane, DMF or dimethyl sulfoxide
- aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 20 ° and 100 ° C.
- the compounds of formula (I) have a wide range of uses. Depending on the selection of the substituents, they can serve as base materials from which liquid-crystalline phases are predominantly composed; However, it is also possible to add compounds of the formula (I) to liquid-crystalline base materials from other classes of compounds in order, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
- the invention also relates to the use of compounds of the formula (I) in liquid-crystal mixtures, preferably ferroelectric and nematic, in particular ferroelectric.
- the invention furthermore relates to liquid crystal mixtures, preferably ferroelectric and nematic, in particular ferroelectric, comprising one or more compounds of the formula (I).
- the liquid crystal mixtures according to the invention generally contain 2 to 35, preferably 2 to 25, particularly preferably 2 to 20 components.
- liquid crystal mixtures which contain compounds of the formula (I) according to the invention are preferably selected from the known compounds with smectic and / or nematic and / or cholesteric phases. These include e.g. B .:
- Phenylbenzoates such as from P. Keller, Ferroelectrics 58
- optically active phenylbenzoates such as those from P. Keller,
- WO-A 93/13093 describes optically active oxirane esters, as described, for example, in EP-A 0 292 954, optically active dioxolane ethers, as described for example in EP-A 0 351 746, optically active dioxolane esters, as described for example in EP-A 0 361 272 described optically active tetrahydrofuran-2-carboxylic acid esters, as described for example in EP-A 0 355 561, and optically active 2-fluoroalkyl ethers, as described for example in EP-A 0 237 007 and US-A 5,051, 506.
- the mixtures in turn can be used in electro-optical or completely optical elements, e.g. B. display elements, switching elements, light modulators, elements for image processing and / or signal processing or generally in the field of non-linear optics.
- Liquid-crystalline mixtures which contain compounds of the general formula (I) are particularly suitable for use in electro-optical switching and display devices (displays). These displays are usually constructed in such a way that a liquid crystal layer is enclosed on both sides by layers which, starting from the LC layer, are usually at least one orientation layer, electrodes and a boundary plate (e.g. made of glass). They also contain spacers, adhesive frames, polarizers and thin color filter layers for color displays. Other possible components are antireflection, passivation, compensation and barrier layers as well as electrically non-linear elements, such as thin-film transistors (TFT) and metal-insulator-metal (MIM) elements.
- TFT thin-film transistors
- MIM metal-insulator-metal
- mixtures for field treatment i.e. H. suitable for operation in quasi-bookshelf geometry (QBG) (see, for example, H. Rieger et al., SID 91 Digest (Anaheim) 1991, 396).
- QBG quasi-bookshelf geometry
- the compounds of the formula (I) can also be used as components of antiferroelectric liquid-crystal mixtures.
- Example 1 1-fluoro-3- (4-hydroxy-phenyl) -7-alkyl-isoquinolines with further alkyl halides, sulfonic acid-2-fluoroalkyl esters, sulfonic acid-2,3- Implement difluoroalkyl esters, sulfonic acid 3-alkyl-oxirane-2-methyl esters, ( ⁇ -bromo-alkyl) cyclopropanes or 1-bromo-dimethylsilanylalkanes.
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Abstract
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DE19517060 | 1995-05-10 | ||
DE19517060A DE19517060A1 (en) | 1995-05-10 | 1995-05-10 | 1-Fluoroisoquinoline derivatives and their use in liquid crystalline mixtures |
PCT/EP1996/001991 WO1996035674A1 (en) | 1995-05-10 | 1996-05-10 | 1-fluorisoquinoline derivatives and the use thereof in liquid crystalline mixtures |
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EP (1) | EP0825987B1 (en) |
JP (1) | JPH11504640A (en) |
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DE19652252A1 (en) * | 1996-12-16 | 1998-06-18 | Hoechst Ag | 1,3-difluoronaphthalene derivatives and their use in liquid crystalline mixtures |
DE19653009A1 (en) * | 1996-12-19 | 1998-06-25 | Hoechst Ag | 6-fluorophenanthridine derivatives and their use in liquid-crystalline mixtures |
EP0916714A1 (en) * | 1997-10-28 | 1999-05-19 | Aventis Research & Technologies GmbH & Co. KG | Chiral smectic liquid crystal mixture containing fluoroisoquinolines |
JP2001316670A (en) * | 2000-05-02 | 2001-11-16 | Dainippon Ink & Chem Inc | Liquid crystal composition |
US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
US7919496B2 (en) | 2004-09-20 | 2011-04-05 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes |
BRPI0515489A (en) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | heterocyclic derivatives and their use as stearoyl coat desaturase inhibitors |
EP1807085B1 (en) | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
JP5094398B2 (en) * | 2004-09-20 | 2012-12-12 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturases |
CA2580781A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-coa-desaturase (scd) |
JP5043668B2 (en) * | 2004-09-20 | 2012-10-10 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | Heterocyclic derivatives and their use as therapeutic agents |
CN101083992A (en) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
MX2007003330A (en) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Pyridine derivatives for inhibiting human stearoyl-coa- desaturase. |
WO2007130075A1 (en) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
CN103200820B (en) | 2010-10-08 | 2016-04-06 | 尼瓦利斯治疗公司 | As the substd quinolines compound of GSNO reductase inhibitor |
BR112013014681A2 (en) | 2010-12-16 | 2016-10-04 | N30 Pharmaceuticals Inc | new substituted bicyclic aromatic compounds as s-nitrosoglutathione reductase inhibitors |
WO2017044766A1 (en) | 2015-09-10 | 2017-03-16 | Nivalis Therapeutics, Inc. | Solid forms of an s-nitrosoglutathione reductase inhibitor |
KR20170074178A (en) * | 2015-12-21 | 2017-06-29 | 제이엔씨 주식회사 | Polymerizable liquid crystal compound, composition, liquid crystal polymerized film-kinds thereof and use thereof |
WO2018107911A1 (en) * | 2016-12-16 | 2018-06-21 | 江苏和成显示科技有限公司 | Liquid crystal compound having negative dielectric anisotropy, and application therefor |
CN108203583B (en) * | 2016-12-16 | 2021-05-25 | 江苏和成显示科技有限公司 | Liquid crystal compound with negative dielectric anisotropy and application thereof |
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US5707547A (en) * | 1993-08-03 | 1998-01-13 | Sumitomo Chemical Company, Limited | Trans-olefin compounds, method for production thereof, liquid crystal composition containing the same as active ingredient, and liquid crystal element using said composition |
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